Honnanayakanavar Jyoti M, Harish Battu, Nanubolu Jagadeesh Babu, Suresh Surisetti
Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500 007, India.
Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201 002, India.
J Org Chem. 2020 Jul 17;85(14):8780-8791. doi: 10.1021/acs.joc.0c00275. Epub 2020 Jul 8.
A copper-catalyzed tandem process integrating regioselective -arylation, followed by aza-Michael addition, is disclosed using 2-aminobenzothiazoles and -halo cinnamic acid congeners. This process generated diverse tetracyclic 5-benzothiazolo[3,2-]quinazoline derivatives in moderate to good yields. The present tandem reaction appears to proceed through concomitant ring opening of 2-aminobenzothiazole and -arylation to give the -cyanamide-substituted diaryl thioether intermediate. The thus generated intermediate likely undergoes an unprecedented Truce-Smiles-type rearrangement involving - to -aryl migration, followed by reformation of the thiazole ring and intramolecular aza-Michael addition to furnish the title products.
公开了一种铜催化的串联过程，该过程结合了区域选择性芳基化，随后进行氮杂迈克尔加成，使用2-氨基苯并噻唑和卤代肉桂酸同系物。该过程以中等至良好的产率生成了多种四环5-苯并噻唑并[3,2-]喹唑啉衍生物。目前的串联反应似乎是通过2-氨基苯并噻唑的伴随开环和芳基化，生成氰基酰胺取代的二芳基硫醚中间体。如此生成的中间体可能经历了前所未有的特鲁茨-斯迈尔斯型重排，涉及从α-到芳基的迁移，随后噻唑环的重新形成和分子内氮杂迈克尔加成，以提供标题产物。
